Textbook Question
Which of the following compounds reacts with HBr more rapidly?
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Ch. 18 - Reactions of Benzene and Substituted Benzenes
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
Chapter 19, Problem 65a
Show how the following compounds can be synthesized from benzene:
a. N,N,N-trimethylanilinium iodide
Verified step by step guidance1
Step 1: Begin with benzene as the starting material. Perform a Friedel-Crafts alkylation reaction using methyl chloride (CH₃Cl) and aluminum chloride (AlCl₃) as a catalyst to introduce a methyl group onto the benzene ring, forming toluene (methylbenzene).
Step 2: Oxidize the methyl group on toluene to a carboxylic acid group using an oxidizing agent such as potassium permanganate (KMnO₄) under acidic or basic conditions. This converts toluene into benzoic acid.
Step 3: Reduce the carboxylic acid group on benzoic acid to an amine group (-NH₂) using a reaction such as the Schmidt reaction or by converting the acid to an amide followed by reduction with lithium aluminum hydride (LiAlH₄). This forms aniline (C₆H₅NH₂).
Step 4: Perform a methylation reaction on the aniline using excess methyl iodide (CH₃I) in the presence of a base such as potassium carbonate (K₂CO₃). This introduces three methyl groups onto the nitrogen atom, forming N,N,N-trimethylaniline.
Step 5: React N,N,N-trimethylaniline with methyl iodide (CH₃I) to quaternize the nitrogen atom, forming N,N,N-trimethylanilinium iodide as the final product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Aromatic Substitution (EAS)
Electrophilic Aromatic Substitution is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the synthesis of N,N,N-trimethylanilinium iodide from benzene, the first step involves the introduction of a nitrogen-containing electrophile, which forms a substituted aromatic compound. This reaction is crucial for modifying aromatic compounds to create more complex structures.
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Quaternization of Amines
Quaternization of amines refers to the process of converting a tertiary amine into a quaternary ammonium salt by reacting it with an alkyl halide. In this case, the nitrogen atom in the aniline derivative formed from benzene is further reacted with methyl iodide to produce N,N,N-trimethylanilinium iodide. This step is essential for achieving the final product with the desired ionic character.
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Nucleophilicity and Electrophilicity
Nucleophilicity refers to the ability of a species to donate an electron pair, while electrophilicity is the ability to accept an electron pair. In the context of the reaction, the nitrogen atom in the amine acts as a nucleophile, attacking the electrophilic carbon of the alkyl halide (methyl iodide). Understanding these concepts is vital for predicting the outcome of reactions involving aromatic compounds and their derivatives.
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Related Practice
Textbook Question
Describe two ways to prepare anisole from benzene.
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Textbook Question
Use the four compounds shown below to answer the following questions:
a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?
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Textbook Question
Show how the following compounds can be synthesized from benzene:
g. p-dideuteriobenzene
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Textbook Question
An aromatic hydrocarbon with a molecular formula of C13H20 has an 1H NMR spectrum with a signal at ~7 ppm that integrates to 5H. It also has two singlets; one of the singlets has 1.5 times the area of the second. What is the structure of the aromatic hydrocarbon?
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Textbook Question
Show how the following compounds can be synthesized from benzene:
h. p-nitro-N-methylaniline
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